This invention relates to novel condensed ring sulfonylureas and their use as herbicides and growth regulants.
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula: ##STR1## wherein R.sub.1 is ##STR2## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA0 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA0 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA0 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA0 W and Q are independently oxygen or sulfur; PA0 n is 0, 1 or 2; PA0 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA0 Y is methyl or methoxy; or their agriculturally suitable salts; provided that: PA0 R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA0 W.sub.1 is O or S; PA0 R is H or CH.sub.3 ; PA0 R.sub.1 is H, F, Cl, Br, CH.sub.3, OCH.sub.3, CF.sub.3, SCH.sub.3 or OCF.sub.2 H; PA0 R.sub.2 is H or C.sub.1 -C.sub.4 alkyl; PA0 R.sub.3 and R.sub.4 are independently H, C.sub.1 -C.sub.4 alkyl, Cl or Br; PA0 R.sub.5 is H or CH.sub.3 ; PA0 R.sub.6 is H or CH.sub.3 ; PA0 R.sub.7 is H or CH.sub.3 ; PA0 A is ##STR14## Y is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, PA0 Z is CH or N; provided that
R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom;
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA1 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA1 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA1 OCF.sub.2 H, SCF.sub.2 H, OCH.sub.2 CF.sub.3, CF.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, PA1 OCH.sub.2 C.tbd.CH, NHCH.sub.3, N(CH.sub.3).sub.2 or CH(OCH.sub.3).sub.2 : and PA1 (a) when W is S, then R is H; PA1 (b) the total number of carbon atoms in R.sub.3 and R.sub.4 L is less than or equal to 4; PA1 (c) when R.sub.5 is CH.sub.3, then n is O; PA1 (d) when J is J.sub.24, then R.sub.4 and R.sub.5 are not both H and R.sub.4 is not Cl or Br; PA1 (e) when Y is OCF.sub.2 H, then Z is CH;
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052g (1959), disclose a number of sulfonamide, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl or ##STR5## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR7## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
Compounds of formula (ii), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974). ##STR8## wherein R is pyridyl.
U.S. Pat. No. 4,169,719 discloses herbicidal benzenesulfonylureas.
Herbicidal indanesulfonylureas are taught in EP-A-82,681, published June 29, 1983.
Herbicidal quinolinesulfonylureas are described in U.S. Pat. No. 4,369,329, issued Jan. 18, 1983.
Herbicidal benzofuran, benzothiophene, benzopyran and benzothiopyran sulfonylureas are disclosed in EP-A-79,683, published May 25, 1983.
EP-A-82,681, published June 29, 1983, discloses herbicidal 1,3-benzodioxole and 1,4-benzodioxanesulfonylureas.
South African patent application No. 835165 discloses herbicidal sulfonylureas of the general structure shown below: ##STR9## wherein A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom, forms a non-aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the --SO-- or SO.sub.2 -- group.
South African patent application No. 837,434 discloses herbicidal sulfonamides of formula ##STR10## where Ar is ##STR11## and R.sub.2 is halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.6 cycloalkyl or C.sub.2 -C.sub.6 alkoxyalkyl.